Not since Justin Bieber and Selena Gomez has there been a more annoying on-again/off-again relationship than the star-crossed romance between Apple and Hollywood.

For those who have clung to the hope that CEO Tim Cook would follow through on his predecessor’s pledge to “crack TV,” the past five years have been painful to watch. One report after another has suggested the tech giant was on the verge of doing a deal with the content companies for some variation on over-the-top video service, only to see nothing materialize.

Which is why it may seem difficult to trust the latest rash of reports that Apple is thisclose to finally launching a Web TV service.

But as often as you’ve been suckered by this tantalizing prospect in the past, forgive yourself if you feel a little more trusting this time around. Reminiscent of that famous “Peanuts” cartoon in which Lucy yanks the football away repeatedly from Charlie Brown, here we are again, lining up for a kick.

Because this time feels, you know, different.

What’s different is that just last week at the unveiling of Apple Watch, Cook made a remark that has to be taken as unambiguous indication he has something up his sleeve a bit bolder than just an Apple TV price reduction. “Apple would reinvent the way you watch TV –and this is only the beginning,” he said during his presentation.

Related

Yes, skeptics, this isn’t the first time Cook has whetted our appetites for Apple invading the TV space. But there’s an even bigger reason the time is nigh to believe he’ll make good on his tease.

When it comes to OTT, the ground is shifting underneath Apple. Instead of being the leader of this new category, the Cupertino colossus finds itself in the uncharacteristic position of being a laggard behind a group of companies that couldn’t hold Steve Jobs’ jock strap: Dish, Sony and Verizon to name a few.

That’s going to force Apple’s hand.

Cook surely understands the risk he is taking by tarrying too much longer: If a competitor somehow manages to bring a product to this market capable of the kind of decisive win that would consign any other comers to me-too status, he will never live it down. Apple’s failure to own TV the way it transformed so many other categories would define his reign no matter what he accomplishes elsewhere–that’s how massive the TV opportunity is.

However, don’t overvalue perception over reality here: It doesn’t really matter that Apple isn’t the first mover in OTT, at least not yet. In these very early days of Sling TV and PlayStation Vue, there is not a market entrant in this space truly generating any heat yet, so Apple won’t be hurt if it is late to the party.

And if by some miracle Sling TV or some similar product does start to take off, the lead taken in that marketplace won’t be so insurmountable that Apple can’t catch up. This is Apple’s power: When Cook decides to throw the company’s hat in a ring, the competitive outlook for that ring is instantly redefined.

To comprehend why any kind of deal here is elusive, it helps to understand the power dynamics between Apple and Hollywood. Hollywood is deathly afraid that Apple will devastate it the way Apple walloped the music industry, which leads to incredibly defensive dealmaking. But Apple is Apple, so emboldened by its own track record that the company isn’t about to have any entity dictate terms of a deal no matter how badly it needs Hollywood’s content.

Immovable object, meet irresistible force.

Given how long Apple and the content companies have been stuck in a perpetual state of inaction, it’s tempting to conclude this just isn’t ever going to happen. Like boxers who do more clinching than punching, this negotiation can be a tiresome sight to behold.

But just because talks have dragged on interminably doesn’t mean there won’t be a positive resolution.

If Guns N’ Roses could finally release “Chinese Democracy,” anything is possible. Who are you going to have more faith in, Axl or Apple?

Sign Up for Daily Insider Newsletter

Not since Justin Bieber and Selena Gomez has there been a more annoying on-again/off-again relationship than the star-crossed romance between Apple and Hollywood. For those who have clung to the hope that CEO Tim Cook would follow through on his predecessor’s pledge to “crack TV,” the past five years have been painful to watch. One […]

Not since Justin Bieber and Selena Gomez has there been a more annoying on-again/off-again relationship than the star-crossed romance between Apple and Hollywood. For those who have clung to the hope that CEO Tim Cook would follow through on his predecessor’s pledge to “crack TV,” the past five years have been painful to watch. One […]

Not since Justin Bieber and Selena Gomez has there been a more annoying on-again/off-again relationship than the star-crossed romance between Apple and Hollywood. For those who have clung to the hope that CEO Tim Cook would follow through on his predecessor’s pledge to “crack TV,” the past five years have been painful to watch. One […]

Not since Justin Bieber and Selena Gomez has there been a more annoying on-again/off-again relationship than the star-crossed romance between Apple and Hollywood. For those who have clung to the hope that CEO Tim Cook would follow through on his predecessor’s pledge to “crack TV,” the past five years have been painful to watch. One […]

Not since Justin Bieber and Selena Gomez has there been a more annoying on-again/off-again relationship than the star-crossed romance between Apple and Hollywood. For those who have clung to the hope that CEO Tim Cook would follow through on his predecessor’s pledge to “crack TV,” the past five years have been painful to watch. One […]

Not since Justin Bieber and Selena Gomez has there been a more annoying on-again/off-again relationship than the star-crossed romance between Apple and Hollywood. For those who have clung to the hope that CEO Tim Cook would follow through on his predecessor’s pledge to “crack TV,” the past five years have been painful to watch. One […]

Not since Justin Bieber and Selena Gomez has there been a more annoying on-again/off-again relationship than the star-crossed romance between Apple and Hollywood. For those who have clung to the hope that CEO Tim Cook would follow through on his predecessor’s pledge to “crack TV,” the past five years have been painful to watch. One […]